U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H34O5
Molecular Weight 354.481
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ALPROSTADIL

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O

InChI

InChIKey=GMVPRGQOIOIIMI-DWKJAMRDSA-N
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H34O5
Molecular Weight 354.481
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Ecraprost [AS 013, Circulase] is a prodrug of prostaglandin E(1) within lipid microspheres that is being developed in Japan by Mitsubishi Pharma Corporation and Asahi Glass. It was originally in development with Welfide Corporation. On 1 October 2001, Welfide Corporation (formerly Yoshitomi) merged with Mitsubishi-Tokyo Pharmaceuticals to form Mitsubishi Pharma Corporation. The new company is a subsidiary of Mitsubishi Chemical. Taisho and Seikagaku Corporation had been involved in the development of ecraprost but discontinued their licences to do so. The effects of ecraprost on reperfusion injury, in preclinical studies, had been reported by Taisho. Ecraprost is in phase II in Japan and was in phase II in Europe for the treatment of peripheral arterial disease. It was also in a phase II study in the treatment of diabetic neuropathies. However, this is no longer an active indication. A phase III trial using a lipid emulsion of ecraprost [Circulase] is underway with Mitsubishi Pharma Corporation in the US, using ecraprost for the treatment of patients with severe peripheral arterial disease, which, because of decreased blood flow to the extremities, can lead to painful ulcers on the legs and feet and subsequent amputation. Alpha Therapeutic Corporation (a former subsidiary of Mitsubishi Pharma) was initially involved in trials of ecraprost in the US, but this responsibility has been taken over by the parent company.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
PROSTIN VR PEDIATRIC

Approved Use

PROSTIN VR PEDIATRIC Sterile Solution is indicated for palliative, not definitive, therapy to temporarily maintain the patency of the ductus arteriosus until corrective or palliative surgery can be performed in neonates who have congenital heart defects and who depend upon the patent ductus for survival. Such congenital heart defects include pulmonary atresia, pulmonary stenosis, tricuspid atresia, tetralogy of Fallot, interruption of the aortic arch, coarctation of the aorta, or transposition of the great vessels with or without other defects.

Launch Date

1981
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.09 pg/mL
20 μg single, intravenous
dose: 20 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALPROSTADIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
174 pg × min/mL
20 μg single, intravenous
dose: 20 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALPROSTADIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.5 min
20 μg single, intravenous
dose: 20 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALPROSTADIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
20 μg single, intravenous
dose: 20 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALPROSTADIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Marked hypotensive and blood flow-increasing effects of a new lipo-PGE(1) (lipo-AS013) due to vascular wall targeting.
2001 Apr 2
Ecraprost: AS 013, Circulase.
2004
Parenteral therapy with lipo-ecraprost, a lipid-based formulation of a PGE1 analog, does not alter six-month outcomes in patients with critical leg ischemia.
2006 Apr
Antiplatelet and anticoagulant drugs for prevention of restenosis/reocclusion following peripheral endovascular treatment.
2012 Aug 15
Patents

Patents

Sample Use Guides

Patients meeting clinical and hemodynamic criteria for critical limb ischemia who were undergoing either bypass or endovascular revascularization of the below knee popliteal or more distal arteries were randomized to receive placebo or a 60-microg dose of lipo-ecraprost administered intravenously starting Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:13:54 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:54 GMT 2023
Record UNII
F5TD010360
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
ALPROSTADIL
EP   INN   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
PROSTAGLANDIN E1 [MI]
Common Name English
ALPROSTADIL [USP MONOGRAPH]
Common Name English
BEFAR
Brand Name English
PROSTIN VR PEDIATRIC
Brand Name English
CAVERJECT
Brand Name English
PRINK
Brand Name English
EDEX
Brand Name English
MUSE
Brand Name English
Alprostadil [WHO-DD]
Common Name English
(1R,2R,3R)-3-Hydroxy-2-[(E)-(3S)-3-hydroxy-1-octenyl]-5-oxocyclopentaneheptanoic acid
Systematic Name English
ALPROSTADIL [USAN]
Common Name English
PROSTAGLANDIN E1
MI  
Common Name English
ALPROSTADIL [MART.]
Common Name English
ONO-1608
Code English
U-10,136
Code English
ALPROSTADIL [JAN]
Common Name English
alprostadil [INN]
Common Name English
PROSTAVASIN
Brand Name English
ALPROSTADIL [USP IMPURITY]
Common Name English
PROST-13-EN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, (11A,13E,15S)-
Common Name English
ALPROSTADIL [USP-RS]
Common Name English
ALPROSTADIL [ORANGE BOOK]
Common Name English
NSC-165559
Code English
U-10136
Code English
PROSTIN
Brand Name English
ALPROSTADIL [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC G04BE01
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
NDF-RT N0000175454
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
NDF-RT N0000007706
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
LOINC 12837-1
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
LOINC 14005-3
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
WHO-VATC QC01EA01
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
FDA ORPHAN DRUG 70092
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
NDF-RT N0000007706
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
NDF-RT N0000180189
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
LOINC 70092-2
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
FDA ORPHAN DRUG 88795
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
WHO-VATC QG04BE01
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
NDF-RT N0000009059
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
NDF-RT N0000007706
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
NDF-RT N0000009911
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
LOINC 2852-2
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
FDA ORPHAN DRUG 95596
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
NDF-RT N0000000106
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
WHO-ATC C01EA01
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
LOINC 70093-0
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
Code System Code Type Description
DAILYMED
F5TD010360
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
CHEBI
15544
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID9022578
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
CAS
745-65-3
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
DRUG CENTRAL
138
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL495
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
RS_ITEM_NUM
1016000
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
NSC
165559
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
MERCK INDEX
m9257
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY Merck Index
INN
4425
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
WIKIPEDIA
PROSTAGLANDIN E1
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
DRUG BANK
DB00770
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
NCI_THESAURUS
C28816
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
NDF-RT
N0000009059
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY Genitourinary Arterial Vasodilation [PE]
FDA UNII
F5TD010360
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
IUPHAR
1882
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
CHEBI
15551
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
NDF-RT
N0000009911
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY Venous Vasodilation [PE]
CHEBI
57397
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
EVMPD
SUB05372MIG
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
PUBCHEM
5280723
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-017-2
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
MESH
D000527
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY
RXCUI
598
Created by admin on Fri Dec 15 15:13:54 GMT 2023 , Edited by admin on Fri Dec 15 15:13:54 GMT 2023
PRIMARY RxNorm
Related Record Type Details
BINDER->LIGAND
BINDING
SUB_CONCEPT->SUBSTANCE
TARGET -> AGONIST
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
DERIVATIVE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
Related Record Type Details
METABOLITE -> PARENT
15-keto-PGE1 has only been detected in vitro in homogenized lung preparations; 15-keto metabolites are less pharmacologically active than the parent compound
IN-VITRO
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
13,14-dihydro-15-ketoprostaglandin E1 is pulmonary metabolite of PGE1 in dogs.
MAJOR
PLASMA
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
15-keto metabolites are less pharmacologically active than the parent compound in vitro using isolated animal organs.
Related Record Type Details
IMPURITY -> PARENT
test 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
test 1
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC